SG181815A1 - Hydrogenation process - Google Patents
Hydrogenation process Download PDFInfo
- Publication number
- SG181815A1 SG181815A1 SG2012045258A SG2012045258A SG181815A1 SG 181815 A1 SG181815 A1 SG 181815A1 SG 2012045258 A SG2012045258 A SG 2012045258A SG 2012045258 A SG2012045258 A SG 2012045258A SG 181815 A1 SG181815 A1 SG 181815A1
- Authority
- SG
- Singapore
- Prior art keywords
- component
- hydrogenation
- composition
- phenol
- hydrogenable
- Prior art date
Links
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 111
- 238000000034 method Methods 0.000 claims abstract description 94
- 239000000203 mixture Substances 0.000 claims abstract description 78
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 64
- 239000003054 catalyst Substances 0.000 claims abstract description 63
- HHNHBFLGXIUXCM-GFCCVEGCSA-N cyclohexylbenzene Chemical compound [CH]1CCCC[C@@H]1C1=CC=CC=C1 HHNHBFLGXIUXCM-GFCCVEGCSA-N 0.000 claims abstract description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 150000001336 alkenes Chemical class 0.000 claims abstract description 21
- 150000002576 ketones Chemical class 0.000 claims abstract description 17
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 78
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 229910052751 metal Inorganic materials 0.000 claims description 29
- 239000002184 metal Substances 0.000 claims description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
- 230000000737 periodic effect Effects 0.000 claims description 12
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 claims description 7
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 6
- WCMSFBRREKZZFL-UHFFFAOYSA-N 3-cyclohexen-1-yl-Benzene Chemical compound C1CCCC(C=2C=CC=CC=2)=C1 WCMSFBRREKZZFL-UHFFFAOYSA-N 0.000 claims description 5
- DRLVMOAWNVOSPE-UHFFFAOYSA-N 2-phenylcyclohexan-1-one Chemical group O=C1CCCCC1C1=CC=CC=C1 DRLVMOAWNVOSPE-UHFFFAOYSA-N 0.000 claims description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 3
- JDTAPZAXMLGOMT-UHFFFAOYSA-N (2-methylcyclopenten-1-yl)benzene Chemical compound C1CCC(C)=C1C1=CC=CC=C1 JDTAPZAXMLGOMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000003647 oxidation Effects 0.000 description 44
- 238000007254 oxidation reaction Methods 0.000 description 44
- ZJMWRROPUADPEA-UHFFFAOYSA-N sec-butylbenzene Chemical compound CCC(C)C1=CC=CC=C1 ZJMWRROPUADPEA-UHFFFAOYSA-N 0.000 description 34
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 238000003776 cleavage reaction Methods 0.000 description 21
- 230000007017 scission Effects 0.000 description 19
- 230000029936 alkylation Effects 0.000 description 18
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 18
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 9
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- 239000000126 substance Substances 0.000 description 9
- -1 CHB peroxide Chemical class 0.000 description 8
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 8
- 229910052809 inorganic oxide Inorganic materials 0.000 description 8
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- GGBJHURWWWLEQH-UHFFFAOYSA-N butylcyclohexane Chemical compound CCCCC1CCCCC1 GGBJHURWWWLEQH-UHFFFAOYSA-N 0.000 description 6
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- 230000002152 alkylating effect Effects 0.000 description 5
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- 239000011230 binding agent Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- OECMNLAWCROQEE-UHFFFAOYSA-N cyclohexylbenzene;hydrogen peroxide Chemical compound OO.C1CCCCC1C1=CC=CC=C1 OECMNLAWCROQEE-UHFFFAOYSA-N 0.000 description 5
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910021536 Zeolite Inorganic materials 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910021393 carbon nanotube Inorganic materials 0.000 description 4
- 239000002041 carbon nanotube Substances 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000010555 transalkylation reaction Methods 0.000 description 4
- 239000010457 zeolite Substances 0.000 description 4
- 239000003377 acid catalyst Substances 0.000 description 3
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- 239000002131 composite material Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000002638 heterogeneous catalyst Substances 0.000 description 3
- 238000010544 hydroalkylation process reaction Methods 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
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- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- 239000004115 Sodium Silicate Substances 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- MPMBRWOOISTHJV-XVNBXDOJSA-N [(e)-but-1-enyl]benzene Chemical compound CC\C=C\C1=CC=CC=C1 MPMBRWOOISTHJV-XVNBXDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
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- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- KHADDDTZDWSVIZ-UHFFFAOYSA-N butan-2-ylbenzene;hydrogen peroxide Chemical compound OO.CCC(C)C1=CC=CC=C1 KHADDDTZDWSVIZ-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
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- 230000001627 detrimental effect Effects 0.000 description 2
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
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- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
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- GNJKALOITRXADZ-OLQVQODUSA-N (3ar,7as)-2-hydroxy-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(O)C(=O)[C@H]21 GNJKALOITRXADZ-OLQVQODUSA-N 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 229910001649 dickite Inorganic materials 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229910052621 halloysite Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229910052680 mordenite Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- ZUSSTQCWRDLYJA-UHFFFAOYSA-N n-hydroxy-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(O)C1=O ZUSSTQCWRDLYJA-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- UHJWZORSTYATLW-UHFFFAOYSA-N o-biphenylyl phenyl ether Natural products C=1C=CC=C(C=2C=CC=CC=2)C=1OC1=CC=CC=C1 UHJWZORSTYATLW-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical group CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 1
- ZRKGTINFVOLLNT-UHFFFAOYSA-N pyrrolo[3,4-b]pyridine-5,7-dione Chemical compound C1=CC=C2C(=O)NC(=O)C2=N1 ZRKGTINFVOLLNT-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- HSSMNYDDDSNUKH-UHFFFAOYSA-K trichlororhodium;hydrate Chemical compound O.Cl[Rh](Cl)Cl HSSMNYDDDSNUKH-UHFFFAOYSA-K 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/08—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by decomposition of hydroperoxides, e.g. cumene hydroperoxide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/19—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings
- C07C29/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings in a non-condensed rings substituted with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/04—Phenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/53—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of hydroperoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30404010P | 2010-02-12 | 2010-02-12 | |
| PCT/US2010/057753 WO2011100013A1 (fr) | 2010-02-12 | 2010-11-23 | Procédé d'hydrogénation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SG181815A1 true SG181815A1 (en) | 2012-07-30 |
Family
ID=44120876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SG2012045258A SG181815A1 (en) | 2010-02-12 | 2010-11-23 | Hydrogenation process |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8658834B2 (fr) |
| EP (1) | EP2534119B1 (fr) |
| KR (1) | KR101431356B1 (fr) |
| CN (1) | CN102741202B (fr) |
| SG (1) | SG181815A1 (fr) |
| TW (2) | TW201623196A (fr) |
| WO (1) | WO2011100013A1 (fr) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8884065B2 (en) | 2010-12-17 | 2014-11-11 | Exxonmobil Chemical Patents Inc. | Process for producing cycloalkylaromatic compounds |
| CN106397132A (zh) | 2011-02-28 | 2017-02-15 | 埃克森美孚化学专利公司 | 制备苯酚的方法 |
| US8981158B2 (en) * | 2011-12-19 | 2015-03-17 | Exxonmobil Chemical Patents Inc. | Oxidation of cyclohexylbenzene |
| CN104271539B (zh) * | 2012-05-03 | 2016-08-24 | 埃克森美孚化学专利公司 | 氢化方法 |
| JP5993525B2 (ja) | 2013-03-04 | 2016-09-14 | エクソンモービル ケミカル パテンツ インコーポレイテッド | シクロヘキシルベンゼンを製造するためのシステム及び方法 |
| EP2964354B1 (fr) * | 2013-03-04 | 2018-05-30 | ExxonMobil Chemical Patents Inc. | Système et procédé de fabrication de phénol et/ou de cyclohéxanone |
| WO2014158978A1 (fr) | 2013-03-25 | 2014-10-02 | Exxonmobil Chemical Patents Inc. | Procédé pour fabriquer un composé aromatique alkylé |
| WO2014158985A1 (fr) | 2013-03-25 | 2014-10-02 | Exxonmobil Chemical Patents Inc. | Procédé de fabrication d'un composé aromatique alkylé |
| SG11201507792XA (en) | 2013-04-02 | 2015-10-29 | Exxonmobil Chem Patents Inc | Process and apparatus for making phenol and/or cyclohexanone |
| US9169170B2 (en) | 2013-10-01 | 2015-10-27 | Exxonmobil Chemical Patents Inc. | Hydroalkylating process |
| US9144792B2 (en) * | 2013-10-23 | 2015-09-29 | Exxonmobil Chemical Patents Inc. | Hydroalkylating process |
| CN105793222A (zh) | 2013-11-22 | 2016-07-20 | 埃克森美孚化学专利公司 | 制造苯酚和/或环己酮的方法 |
| CN105829272A (zh) | 2013-12-20 | 2016-08-03 | 埃克森美孚化学专利公司 | 苯酚组合物 |
| US10259759B2 (en) | 2013-12-20 | 2019-04-16 | Exxonmobil Chemical Patents Inc. | Cyclohexylbenzene composition |
| US9908829B2 (en) | 2013-12-20 | 2018-03-06 | Exxonmobil Chemical Patents Inc. | Process for making phenol and/or cyclohexanone |
| WO2015183384A1 (fr) | 2014-05-30 | 2015-12-03 | Exxonmobil Chemical Patents Inc. | Procédé et dispositif pour éliminer l'eau et/ou l'oxygène d'un liquide organique |
| EP3180302B1 (fr) | 2014-08-15 | 2019-01-30 | ExxonMobil Chemical Patents Inc. | Procédé de fabrication de cyclohexanone |
| EP3180305A1 (fr) | 2014-08-15 | 2017-06-21 | ExxonMobil Chemical Patents Inc. | Procédé et système pour la fabrication de cyclohexanone |
| US9926254B2 (en) | 2014-08-15 | 2018-03-27 | Exxonmobil Chemical Patents Inc. | Process and system for making cyclohexanone |
| WO2016025217A1 (fr) | 2014-08-15 | 2016-02-18 | Exxonmobil Chemical Patents Inc. | Procédé et système pour la fabrication de cyclohexanone |
| US9868687B2 (en) | 2014-09-30 | 2018-01-16 | Exxonmobil Chemical Patents Inc. | Process for making cyclohexanone |
| US10294178B2 (en) | 2015-03-31 | 2019-05-21 | Exxonmobil Chemical Patents Inc. | Process for making cyclohexanone and/or phenol |
| US10259765B2 (en) | 2015-07-31 | 2019-04-16 | Exxonmobil Chemical Patents Inc. | Process for making cyclohexanone |
| WO2017023429A1 (fr) | 2015-07-31 | 2017-02-09 | Exxonmobil Chemical Patents Inc. | Procédé de production de cyclohexanone |
| JP2019513788A (ja) | 2016-04-13 | 2019-05-30 | エクソンモービル ケミカル パテンツ インコーポレイテッド | メチル置換ビフェニル化合物の製造 |
| WO2017180240A1 (fr) * | 2016-04-13 | 2017-10-19 | Exxonmobil Chemilcal Patents Inc. | Production de composés biphényle substitués par un groupe méthyle |
| WO2019005276A1 (fr) | 2017-06-28 | 2019-01-03 | Exxonmobil Chemical Patents Inc. | Produits contenant du cyclohexanone et procédés de fabrication de ceux-ci |
| US10941099B2 (en) | 2017-06-28 | 2021-03-09 | Exxonmobil Chemical Patents Inc. | Cyclohexanone-containing products and processes for making the same |
| US10752570B2 (en) | 2017-06-28 | 2020-08-25 | Exxonmobil Chemical Patents Inc. | Processes for making cyclohexanone |
| WO2019036119A1 (fr) | 2017-08-18 | 2019-02-21 | Exxonmobil Chemical Patents Inc. | Procédé d'hydroperoxydation de cyclohexylbenzène et procédé de fonctionnement d'un réacteur d'oxydation |
| CN110898853B (zh) * | 2019-12-19 | 2022-05-17 | 太原理工大学 | 一种苯酚加氢制备环己酮的催化剂及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4021490A (en) | 1975-10-14 | 1977-05-03 | Phillips Petroleum Company | Process for production of phenol and cyclohexanone |
| US4019965A (en) | 1976-07-20 | 1977-04-26 | Phillips Petroleum Company | Separation of phenol, cyclohexanone, and cyclohexylbenzene containing mixtures employing dialkyl and dicycloalkyl phthalates |
| US4016049A (en) | 1976-07-28 | 1977-04-05 | Phillips Petroleum Company | Separation of phenol-cyclohexanone azeotrope by extractive distillation with adipic acid diester |
| US4115204A (en) | 1977-07-21 | 1978-09-19 | Phillips Petroleum Company | Separation of phenol-, cyclohexanone-, and cyclohexylbenzene-containing mixtures employing an N,N-disubstituted amide |
| US4115206A (en) | 1977-07-21 | 1978-09-19 | Phillips Petroleum Company | Separation of phenol-, cyclohexanone-, and cyclohexylbenzene-containing mixtures employing an organic carbonate |
| US4115205A (en) | 1977-07-21 | 1978-09-19 | Phillips Petroleum Company | Separation of phenol-, cyclohexanone-, and cyclohexylbenzene-containing mixtures employing an N-substituted lactam |
| US4115207A (en) | 1977-07-27 | 1978-09-19 | Phillips Petroleum Company | Separation of phenol-, cyclohexanone-, and cyclohexylbenzene-containing mixtures employing a trisubstituted phosphate |
| US4169857A (en) * | 1978-10-05 | 1979-10-02 | Phillips Petroleum Company | Separation of cyclohexylbenzene-cyclohexanone-phenol-containing mixtures by hydrogenation and distillation |
| US4167456A (en) | 1978-10-06 | 1979-09-11 | Phillips Petroleum Co. | Extractive distillation to separate cyclohexylbenzene from phenol-cyclohexanone mixture containing the same |
| US4201632A (en) | 1978-12-20 | 1980-05-06 | Phillips Petroleum Company | Separation of phenol-, cyclohexanone-, and cyclohexylbenzene-containing mixtures employing a nitrile as extraction distillation solvent |
| US4230638A (en) | 1979-05-04 | 1980-10-28 | Phillips Petroleum Company | Separation of cyclohexylbenzene from a cyclohexylbenzene-cyclohexanone-phenol admixture |
| DE3117135A1 (de) | 1981-04-30 | 1982-11-18 | Bayer Ag, 5090 Leverkusen | Kristallines alumosilicat, verfahren zu dessen herstellung sowie dessen verwendung zur katalytischen umwandlung von methanol und/oder dimethylether in kohlenwasserstoffe |
| US4826667A (en) | 1986-01-29 | 1989-05-02 | Chevron Research Company | Zeolite SSZ-25 |
| US4954325A (en) | 1986-07-29 | 1990-09-04 | Mobil Oil Corp. | Composition of synthetic porous crystalline material, its synthesis and use |
| IT1205681B (it) | 1987-05-26 | 1989-03-31 | Eniricerche Spa | Materiale sintetico cristallino poroso contenente ossidi di silicio e boro |
| US4870217A (en) | 1988-10-24 | 1989-09-26 | Texaco Chemical Company | Method for production of phenol/acetone from cumene hydroperoxide |
| US5250277A (en) | 1991-01-11 | 1993-10-05 | Mobil Oil Corp. | Crystalline oxide material |
| US5236575A (en) | 1991-06-19 | 1993-08-17 | Mobil Oil Corp. | Synthetic porous crystalline mcm-49, its synthesis and use |
| DE4205633A1 (de) | 1992-02-25 | 1993-08-26 | Bayer Antwerpen Nv | Verfahren zur reinigung von cyclohexanon |
| US5362697A (en) | 1993-04-26 | 1994-11-08 | Mobil Oil Corp. | Synthetic layered MCM-56, its synthesis and use |
| ES2124154B1 (es) | 1995-11-08 | 1999-12-01 | Univ Politecnica De Valencia C | Metodo de preparaciion y propiedades cataliticas de un solido microporoso con alta superficie externa. |
| ES2105982B1 (es) | 1995-11-23 | 1998-07-01 | Consejo Superior Investigacion | Zeolita itq-1 |
| TW382146B (en) | 1998-06-19 | 2000-02-11 | United Microeletronics Corp | Semiconductor step-down voltage device having low power consumption |
| US6037513A (en) | 1998-07-09 | 2000-03-14 | Mobil Oil Corporation | Hydroalkylation of aromatic hydrocarbons |
| DE10015874A1 (de) | 2000-03-30 | 2001-10-11 | Creavis Tech & Innovation Gmbh | Verfahren zur Herstellung von aromatischen Alkoholen insbesondere Phenol |
| US6756030B1 (en) | 2003-03-21 | 2004-06-29 | Uop Llc | Crystalline aluminosilicate zeolitic composition: UZM-8 |
| US7199271B2 (en) | 2005-03-17 | 2007-04-03 | Invista North America S.A.R.L. | Method for reducing cyclohexenone content of a cyclohexenone-containing organic mixture |
| WO2008101616A1 (fr) * | 2007-02-22 | 2008-08-28 | Exxonmobil Chemical Patents Inc. | Fabrication de composés alkylaromatiques |
| EP2200955B1 (fr) | 2007-09-21 | 2011-04-20 | ExxonMobil Chemical Patents Inc. | Procede de fabrication de cyclohexylbenzene |
| JP5386584B2 (ja) | 2008-08-29 | 2014-01-15 | エクソンモービル・ケミカル・パテンツ・インク | フェノールの製造方法 |
-
2010
- 2010-11-23 WO PCT/US2010/057753 patent/WO2011100013A1/fr active Application Filing
- 2010-11-23 US US13/516,414 patent/US8658834B2/en not_active Expired - Fee Related
- 2010-11-23 EP EP10784929.1A patent/EP2534119B1/fr not_active Not-in-force
- 2010-11-23 CN CN201080062961.5A patent/CN102741202B/zh not_active Expired - Fee Related
- 2010-11-23 SG SG2012045258A patent/SG181815A1/en unknown
- 2010-11-23 KR KR1020127021163A patent/KR101431356B1/ko not_active IP Right Cessation
- 2010-11-25 TW TW105108817A patent/TW201623196A/zh unknown
- 2010-11-25 TW TW099140785A patent/TWI547476B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| KR20120116480A (ko) | 2012-10-22 |
| US20120277472A1 (en) | 2012-11-01 |
| EP2534119B1 (fr) | 2017-04-05 |
| US8658834B2 (en) | 2014-02-25 |
| EP2534119A1 (fr) | 2012-12-19 |
| TW201623196A (zh) | 2016-07-01 |
| WO2011100013A1 (fr) | 2011-08-18 |
| CN102741202B (zh) | 2015-11-25 |
| CN102741202A (zh) | 2012-10-17 |
| TWI547476B (zh) | 2016-09-01 |
| KR101431356B1 (ko) | 2014-08-19 |
| TW201132623A (en) | 2011-10-01 |
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